Chemical Properties
Pale Yellow Solid
Originator
Pivalone,Jouveinal,France,1978
Uses
Free thiol in chemoaffinity labeling.
Uses
Tixocortol 21-Pivalate is an anti-inflammatory agent. Tixocortol 21-Pivalate is used in fluorescent chemoaffinity labeling.
Uses
Anti-inflammatory. Used in fluorescent chemoaffinity labeling.
Definition
ChEBI: The pivalate thioester of tixocortol.
Manufacturing Process
In a reactor of 50 liters, sodium S-thiopivalate is prepared from 100 g of S_x0002_thiopivalic acid (0.844 mol), 214 cc of solution of sodium methylate, 3.95 M
(0.844 mol) in 25 liters of anhydrous acetone.
There are then added 285 g (0.603 mol) of dihydroxy-11β,17α-iodo-21-dioxo-
3,20-pregnene-4 and the mixture is brought up to the acetone reflux for two
hours. The solvent is eliminated by distillation under vacuum until there is
obtained a syrupy residue which is poured into 10 liters of iced water. The
insoluble part is filtered and dried under vacuum.
The crude product is purified by recrystallization from ethanol; weight: 250 g;
yield: 89.5%.
Therapeutic Function
Antiinflammatory
Contact allergens
Tixocortol 21-pivalate is a 21-ester of tixocortol, widely
used in topical treatments. It can induce severe allergic
contact dermatitis. This corticosteroid is a marker of the
allergenic A group that includes molecules without
major substitution on the D cycle (no C 16 methylation,
no C 17 side chain). A short-chain C 21 ester is possible.
Molecules are cloprednol, cortisone, fludrocortisone,
fluorometholone, hydrocortisone, methylprednisolone,
methylprednisone, prednisolone, prednisone, tixocor-
tol, and their C 21 esters (acetate, caproate or hexanoate,
phosphate, pivalate or trimethylacetate, succinate or
hemisuccinate, m-sulfobenzoate).